Or that they won't be dealing with their entrenched, non paying tenant, or relative or the hoarder house in their life time.  

I did deed intel on the area and if I was not so well entrenched in Portland I would move there.Fast forward and 8 flips later and 9 new constructions going right now this is one of the best markets in the country.

Generally speaking, you want to target communities that welcome growth of all sorts, and are willing to make the necessary tradeoffs to support it, occasionally at the expense of entrenched interests.

Just look at how hard the currently entrenched (anti-competitive) industries are fighting Uber and Airbnb.

I got more entrenched in work, deal were still falling through left and right, tenants were vandalizing my property with no regard, I was still technically homeless and the IRS decided to freeze my accounts.

I think politicians who are well-entrenched have a certain arrogance that causes them to behave as if they are above the law.This arrogance seems to trickle down to all levels of government employees, many of whom behave as if they are doing us a favor when they are doing their jobs.What happened to the concept of a public "servant."

Entrenched, hoarding tenants only get worse with time (and age).

but looking broadly for two things:1) Anybody else run into zoning / planning issues where you felt like there was sort of an entrenched opinion you had to work through, how'd you do it?

Hmm cheap money and a tech based algorithm and a failed attempt to disrupt an entrenched business model.

Specifically, take a hard look at Detroit.It's still flying under the radar right now, largely because people dismiss it due to entrenched negative perceptions that no longer hold true.